ch 18 - CHAPTER 18 Review of 140B R i f Enols, Enols...

Info iconThis preview shows pages 1–5. Sign up to view the full content.

View Full Document Right Arrow Icon
CHAPTER 18 Review of 140B Enols Enolates and the Aldol Enols, Enolates and the Aldol Condensation: α β -Unsaturated Aldehydes and α , β Unsaturated Aldehydes and Ketones Strong bases can remove α hydrogens leading to anions called enolate ions or enolates or .
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Enol formation leads to deuterium exchange Enol formation leads to deuterium exchange. Enol formation leads to racemization Cat. Cat. Enol formation leads to racemization.
Background image of page 2
Aldehydes and ketones react with halogens at their α -carbons. Further halogenation is slow because the electron-withdrawing halogen substituent makes enolization more difficult. Singly halogenated product molecules are not attacked until all of Singly halogenated product molecules are not attacked until all of the starting aldehyde or ketone has been used up.
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Alkylation of Enolates - Side Reactions: Regioisomeric Products: If the starting ketone is unsymmetrical, either α -carbon may be alkylated. Multiple Alkylations: Even ketones may lose a second
Background image of page 4
Image of page 5
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 12/26/2008 for the course CHEM CHEM 140C taught by Professor Finn during the Spring '08 term at UCSD.

Page1 / 10

ch 18 - CHAPTER 18 Review of 140B R i f Enols, Enols...

This preview shows document pages 1 - 5. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online